Tetrabutylammonium Fluoride → HCID 90310848, compound

HRID 1519171Notes

Reaction equation

HRID 1519171 reaction equation
[Si]([O:8][C:9]1[C:10]([F:23])=[C:11]([C:16]2[N:17]=[CH:18][C:19]([NH2:22])=[N:20][CH:21]=2)[CH:12]=[CH:13][C:14]=1[CH3:15])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[NH2:22][C:19]1[N:20]=[CH:21][C:16]([C:11]2[C:10]([F:23])=[C:9]([OH:8])[C:14]([CH3:15])=[CH:13][CH:12]=2)=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90310783HCID 90310783, compound

Product 1

HCID 90310848HCID 90310848, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(3-((tert-Butyldimethylsilyl)oxy)-2-fluoro-4-methylphenyl)pyrazin-2-amine (342 mg, 1.03 mmol) was dissolved in THF (1.2 mL) at rt and then treated with tetrabutylammonium fluoride (1.2 mL, 1 M in THF). The reaction was stirred for 1 hour at rt, before diluting with water (10 mL) and extracting with EtOAc (10 mL×4). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by FCC to provide the title compound. 1H NMR (500 MHz, CD3OD) δ 8.26 (dd, J=2.3, 1.5, 1H), 8.01 (d, J=1.5, 1H), 7.09 (m, 1H), 6.94 (m, 1H), 2.25 (s, 3H).

Workup

  1. extractionextracting with EtOAc (10 mL×4)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-bbb10f5a7e324b24a9c1a64b61b5b5ec
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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